GB1534903A - Process for the preparation of arylene sulphide polymers - Google Patents
Process for the preparation of arylene sulphide polymersInfo
- Publication number
- GB1534903A GB1534903A GB21882/76A GB2188276A GB1534903A GB 1534903 A GB1534903 A GB 1534903A GB 21882/76 A GB21882/76 A GB 21882/76A GB 2188276 A GB2188276 A GB 2188276A GB 1534903 A GB1534903 A GB 1534903A
- Authority
- GB
- United Kingdom
- Prior art keywords
- mixture
- alkyl
- pyrrolidone
- water
- polymers
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/025—Preparatory processes
- C08G75/0254—Preparatory processes using metal sulfides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/0231—Polyarylenethioethers containing chain-terminating or chain-branching agents
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
1534903 Arylene sulfide polymers PHILLIPS PETROLEUM CO 26 May 1976 [27 May 1975 19 Jan 1976] 21882/76 Heading C3R Arylene sulfide polymers are prepared by a process which comprises reacting together: (i) one or more p-dihalo-benzenes or substituted pdihalobenzenes of the formula where X is Cl, Br or I, and R is hydrogen or a saturated or aromatic hydrocarbyl radical, e.g. alkyl, cycloalkyl, aryl, alkaryl or aralkyl radicals, the total number of carbon atoms in each molecule being from 6-24, with the proviso that at least 50 mol. per cent of the reactant is constituted by p-dihalobenzene, i.e. compounds of the above formula where each R is hydrogen; (ii) an alkali metal sulfide; and (iii) lithium acetate; the reaction being performed in the presence of an N-alkyl-2-pyrrolidone of the formula where R<SP>1</SP> is H or C 1 -C 3 alkyl, and R<SP>11</SP> is C 1 -C 3 alkyl, the total number of carbon atoms in the molecule being from 5-8, and at a temperature of 125 to 450 C.; wherein the reactants are brought together in the following sequence: (a) forming a first mixture containing lithium acetate, N-alkyl-2-pyrrolidone and water in free form or as water of hydration; (b) dehydrating the mixture generally by distillation; (c) adding to the dehydrated mixture an aqueous composition containing the alkali metal sulfide, and optionally an alkali metal hydroxide or alkali metal carbonate, and up to 50% wt. based on the weight of said aqueous composition, of water in free form and/or as water of hydration; (d) dehydrating the mixture generally by distillation, and (e) adding the dihalobenzene to the dehydrated mixture formed in step (d). There may optionally be added to the reaction mix in step (e) up to 0À6 p.b.w. per 100 p.b.w. of reactant (i) of a polyhaloaromatic compound of the formula R<SP>111</SP>X n where X is Cl, Br or I, n is 3-6, and R<SP>111</SP> is a polyvalent aromatic radical of valence n, having one or more aromatic rings, which may be fused together or separate and may contain up to 4 methyl substituents, the total number of carbon atoms in the compound being from 6-16. At the end of the polymerization reaction the N-alkyl-2-pyrrolidone may be distilled from the reaction mixture, in which case carbon dioxide is preferably introduced into the reaction mixture during or after the polymerization reaction but before the distillation of the N-alkyl-2-pyrrolidone. Alternatively the arylene sulfide polymers may be separated from the reaction mixture by filtration, or by dilution of the reaction mixture with water, followed by filtration. The polymers may be blended with fillers, pigments, extenders and other polymers and cured through crosslinking and/or chain extension, e.g. by heating up to 480 C. in the presence of a free-oxygen containing gas. In the Examples poly(p-phenylene sulphides) are prepared as above by first dehydrating a mixture of lithium acetate dihydrate and N-methyl-2-pyrrolidone, then adding thereto sodium sulfide, sodium hydroxide and water, and then dehydrating the resultant mixture, and then adding p-dichlorobenzene and N-methyl-2-pyrrolidone and optionally 1,2,4-trichlorobenzene and then polymerizing. Uses.-Coatings, films, fibres and moulded objects.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US58133175A | 1975-05-27 | 1975-05-27 | |
US05/642,098 US4064114A (en) | 1975-05-27 | 1976-01-19 | Production of arylene sulfide polymers |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1534903A true GB1534903A (en) | 1978-12-06 |
Family
ID=27078291
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB21882/76A Expired GB1534903A (en) | 1975-05-27 | 1976-05-26 | Process for the preparation of arylene sulphide polymers |
Country Status (11)
Country | Link |
---|---|
JP (1) | JPS51144496A (en) |
CA (1) | CA1087348A (en) |
DE (1) | DE2623333C2 (en) |
DK (1) | DK156224C (en) |
ES (1) | ES448119A1 (en) |
FR (1) | FR2312525A1 (en) |
GB (1) | GB1534903A (en) |
IT (1) | IT1061399B (en) |
NL (1) | NL167448C (en) |
NO (1) | NO140890C (en) |
SE (1) | SE414638B (en) |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4116947A (en) * | 1977-04-29 | 1978-09-26 | Phillips Petroleum Company | Branched arylene sulfide polymer production |
DE3019732A1 (en) * | 1980-05-23 | 1981-12-03 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING POLYARYL SULFIDES |
JPS57137346A (en) * | 1981-02-18 | 1982-08-24 | Toray Ind Inc | Thermoplastic polyester resin |
JPS58206632A (en) * | 1982-05-28 | 1983-12-01 | Dainippon Ink & Chem Inc | Preparation of polyphenylene sulfide |
AU544880B2 (en) * | 1982-08-03 | 1985-06-20 | Phillips Petroleum Co. | Arylene sulphide terpolymers |
JPS5925822A (en) * | 1982-08-04 | 1984-02-09 | Dainippon Ink & Chem Inc | Preparation of polyphenylene sulfide |
DE3243189A1 (en) * | 1982-11-23 | 1984-05-24 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING HIGHLY MOLECULAR, OR optionally BRANCHED POLYARYL SULFIDES |
DE3312284A1 (en) * | 1983-04-05 | 1984-10-11 | Bayer Ag, 5090 Leverkusen | METHOD FOR THE PRODUCTION OF POLYARYL SULFIDES BRANCHED, IF ANY |
DE3312254A1 (en) * | 1983-04-05 | 1984-10-11 | Bayer Ag, 5090 Leverkusen | METHOD FOR THE PRODUCTION OF POLYARYL SULFIDES BRANCHED, IF ANY |
DE3318401A1 (en) * | 1983-05-20 | 1984-11-22 | Bayer Ag, 5090 Leverkusen | METHOD FOR THE PRODUCTION OF HIGH MOLECULAR POLYARYL SULFIDES, BRANCHED IF NEEDED |
DE3339233A1 (en) * | 1983-10-28 | 1985-05-09 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING OPTIONALLY BRANCHED POLYARYL SULFIDES WITH REDUCED CORROSIVITY |
JPS60119277U (en) * | 1984-01-20 | 1985-08-12 | 林 利雄 | Patsukin assembles a cylinder into a triangular pyramid |
DE3426918A1 (en) * | 1984-07-21 | 1986-01-23 | Bayer Ag, 5090 Leverkusen | FIBER REINFORCED POLYPHENYLENE SULFIDE |
DE3428985A1 (en) * | 1984-08-07 | 1986-02-20 | Bayer Ag, 5090 Leverkusen | Process for the preparation of high-molecular weight, optionally branched polyarylene sulphides |
DE3428986A1 (en) * | 1984-08-07 | 1986-02-20 | Bayer Ag, 5090 Leverkusen | METHOD FOR THE PRODUCTION OF HIGH MOLECULAR POLYARYL SULFIDES, BRANCHED IF NEEDED |
DE3428984A1 (en) * | 1984-08-07 | 1986-02-20 | Bayer Ag, 5090 Leverkusen | METHOD FOR THE PRODUCTION OF HIGH MOLECULAR POLYARYL SULFIDES, BRANCHED IF NEEDED |
JPH0649761B2 (en) * | 1985-12-18 | 1994-06-29 | 東ソー株式会社 | Method for producing polyphenylene sulphide |
JPS6353260U (en) * | 1986-09-24 | 1988-04-09 | ||
JP2792653B2 (en) * | 1988-04-28 | 1998-09-03 | 東ソー株式会社 | Method for producing polyphenylene sulfide |
CA2102477A1 (en) * | 1992-11-24 | 1994-05-25 | Paul J. Deslauriers | Compositions comprising sulfur-containing derivatives of hydroxyphenylbenzotriazole and process therefor |
WO2020044819A1 (en) | 2018-08-29 | 2020-03-05 | 株式会社クレハ | Continuous dehydration method and method for producing polyarylene sulfide |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3354129A (en) * | 1963-11-27 | 1967-11-21 | Phillips Petroleum Co | Production of polymers from aromatic compounds |
DE2053313A1 (en) * | 1970-10-30 | 1972-05-04 | Hess Sb Automatenbau Gmbh | Brewing device for coffee machine |
US3763124A (en) * | 1971-06-21 | 1973-10-02 | Phillips Petroleum Co | Treatment of the alkali metal sulfide reactant to reduce impurities and its reaction with a polyhalo substituted aromatic compound |
US3786035A (en) * | 1972-05-15 | 1974-01-15 | Phillips Petroleum Co | Alkali metal sulfide-arylene sulfide polymer process |
-
1976
- 1976-03-04 CA CA247,086A patent/CA1087348A/en not_active Expired
- 1976-05-20 JP JP51058456A patent/JPS51144496A/en active Granted
- 1976-05-21 ES ES448119A patent/ES448119A1/en not_active Expired
- 1976-05-24 NO NO761764A patent/NO140890C/en unknown
- 1976-05-25 DE DE2623333A patent/DE2623333C2/en not_active Expired
- 1976-05-26 IT IT23698/76A patent/IT1061399B/en active
- 1976-05-26 NL NL7605676.A patent/NL167448C/en not_active IP Right Cessation
- 1976-05-26 GB GB21882/76A patent/GB1534903A/en not_active Expired
- 1976-05-26 DK DK231076A patent/DK156224C/en not_active IP Right Cessation
- 1976-05-26 FR FR7616017A patent/FR2312525A1/en active Granted
- 1976-05-26 SE SE7606021A patent/SE414638B/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
ES448119A1 (en) | 1977-07-01 |
FR2312525B1 (en) | 1979-08-17 |
NL167448B (en) | 1981-07-16 |
DK156224B (en) | 1989-07-10 |
DK231076A (en) | 1976-11-28 |
NO140890C (en) | 1979-12-05 |
DE2623333C2 (en) | 1982-12-02 |
CA1087348A (en) | 1980-10-07 |
JPS51144496A (en) | 1976-12-11 |
NO761764L (en) | 1976-11-30 |
IT1061399B (en) | 1983-02-28 |
SE7606021L (en) | 1976-11-28 |
NO140890B (en) | 1979-08-27 |
NL167448C (en) | 1981-12-16 |
SE414638B (en) | 1980-08-11 |
JPS5325589B2 (en) | 1978-07-27 |
DK156224C (en) | 1989-11-20 |
NL7605676A (en) | 1976-11-30 |
FR2312525A1 (en) | 1976-12-24 |
DE2623333A1 (en) | 1976-12-09 |
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EP0033906B1 (en) | Process for the production of aromatic sulfide/sulfone polymers | |
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GB1600911A (en) | Process for the preparation of arylene sulfide polymers | |
CA1113645A (en) | Aromatic sulfide/sulfone polymer production | |
CA1196147A (en) | Arylene sulfide polymer preparation | |
DE3312254A1 (en) | METHOD FOR THE PRODUCTION OF POLYARYL SULFIDES BRANCHED, IF ANY | |
US4125525A (en) | Aromatic sulfide/sulfone polymer production | |
US5015702A (en) | Treatment of poly(arylene sulfide/sulfone) polymers | |
US5008368A (en) | Preparation of poly(arylene sulfide/sulfone) polymer with addition of water after polymerization is initiated | |
JPS63170422A (en) | Production of polyarylene sulfide | |
US2831896A (en) | Compositions of polythiols and method of making the same | |
JPS59219332A (en) | Production of polyphenylene sulfide | |
US3367975A (en) | Process for preparing organic disulfides from tetrathiocarbonates and alkyl halides | |
JPS62190228A (en) | Production of polyarylene sulfide | |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19930526 |